JP3081065B2 - Novel amine and its production method - Google Patents
Novel amine and its production methodInfo
- Publication number
- JP3081065B2 JP3081065B2 JP04175264A JP17526492A JP3081065B2 JP 3081065 B2 JP3081065 B2 JP 3081065B2 JP 04175264 A JP04175264 A JP 04175264A JP 17526492 A JP17526492 A JP 17526492A JP 3081065 B2 JP3081065 B2 JP 3081065B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- reaction
- amino alcohol
- represented
- temperature
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は新規なアミン及びその製
造法に関するものである。更に詳しくは、界面活性剤、
更には布、毛髪などの柔軟剤として使用される新規なア
ミン及びその製造法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel amine and a method for producing the same. More specifically, a surfactant,
Further, the present invention relates to a novel amine used as a softener for fabric, hair, etc., and a method for producing the same.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】従来、
布及び毛髪等の柔軟剤として使用されている化合物は、
アルキル基を有する第４級アンモニウム塩であるが、生
分解性のより優れた柔軟剤を開発する必要がある。従っ
て、本発明の課題は、柔軟性に優れかつ生分解性のより
優れた柔軟剤として適した化合物を得ることである。2. Description of the Related Art
Compounds used as softeners for fabrics and hair,
Although it is a quaternary ammonium salt having an alkyl group, it is necessary to develop a softener having better biodegradability. Therefore, an object of the present invention is to obtain a compound suitable as a softener having excellent flexibility and more excellent biodegradability.
【０００３】[0003]
【課題を解決するための手段】本発明者らは、上記課題
を解決すべく鋭意検討した結果、特定の新規アミンが上
記目的に最適であることを見いだし、本発明を完成し
た。すなわち、本発明は、一般式（Ｉ）で表されるアミ
ン及びその製造法を提供するものである。Means for Solving the Problems The present inventors have conducted intensive studies to solve the above problems, and as a result, have found that a specific novel amine is most suitable for the above purpose, and have completed the present invention. That is, the present invention provides an amine represented by the general formula (I) and a method for producing the same.
【０００４】[0004]
【化５】 Embedded image
【０００５】〔式中、R1：炭素数７〜35の直鎖又は分岐
鎖のアルキル基又はアルケニル基を示し、２つのR1は同
一でも異なっていても良い。 X ：−CR＜又は−N＜を示す。ここでRはH 又は炭素数１
〜４のアルキル基を示す。 k ：１〜３の数を示す。 p ：０〜９の数を示す。 m、n ：同一又は異なって０〜４の数を示す。但し m及
びn が同時に０になることはない。〕 一般式（Ｉ）で表されるアミンとしては例えば次のよう
なものが挙げられる。[Wherein, R 1 represents a linear or branched alkyl or alkenyl group having 7 to 35 carbon atoms, and two R 1 s may be the same or different. X: represents -CR <or -N <. Where R is H or carbon number 1
And represents alkyl groups 4 to 4. k: Indicates the number of 1 to 3. p: Indicates the number of 0-9. m, n: same or different, and represents a number of 0-4. However, m and n do not become 0 at the same time. Examples of the amine represented by the general formula (I) include the following.
【０００６】[0006]
【化６】 Embedded image
【０００７】一般式（Ｉ）で表される本発明のアミン
（以下アミン（Ｉ）と略記する）は、次の方法により製
造される。一般式（II）The amine of the present invention represented by the general formula (I) (hereinafter abbreviated as amine (I)) is produced by the following method. General formula (II)
【０００８】[0008]
【化７】 Embedded image
【０００９】〔式中、X 、p 、m 、n は前記の意味を示
す。〕で表されるアミノアルコール（以下アミノアルコ
ール（II）と略記する）にアクリロニトリルを用いてシ
アノエチル化反応、ついで触媒を用いて水素化反応を行
い、一般式（III)[Wherein, X, p, m, and n have the above-mentioned meanings. To an amino alcohol (hereinafter abbreviated as amino alcohol (II)) represented by the general formula (III) by a cyanoethylation reaction using acrylonitrile and a hydrogenation reaction using a catalyst.
【００１０】[0010]
【化８】 Embedded image
【００１１】〔式中、X 、p 、m 、n は前記の意味を示
す。〕で表されるアミノアルコール（以下アミノアルコ
ール(III) と略記する）とし、必要であればアクリロニ
トリルを用いるシアノエチル化反応及び水素化反応を繰
り返し、一般式（IV）[Wherein, X, p, m, and n have the above-mentioned meanings. And repeating, if necessary, a cyanoethylation reaction and a hydrogenation reaction using acrylonitrile, to obtain an amino alcohol (abbreviated as amino alcohol (III)) represented by the following general formula (IV):
【００１２】[0012]
【化９】 Embedded image
【００１３】〔式中、X 、p 、m 、n は前記の意味を示
し、q は２〜３の数を示す。〕で表されるアミノアルコ
ール（以下アミノアルコール (IV) と略記する）を得、
得られたアミノアルコール（III)又は（IV）を一般式
（Ｖ） R1COOR2 （Ｖ） 〔式中、R1は前記の意味を示し、R2はH 又は炭素数１〜
３のアルキル基を示す。〕で表される脂肪酸又はそのエ
ステル（以下脂肪酸又はそのエステル（Ｖ）と略記す
る）でアシル化を行い、アミン（Ｉ）を得る。[Wherein, X, p, m, and n have the above-mentioned meanings, and q represents a number of 2-3. ] (Hereinafter abbreviated as amino alcohol (IV))
The obtained amino alcohol (III) or (IV) is represented by the general formula (V) R 1 COOR 2 (V) wherein R 1 has the above-mentioned meaning, and R 2 is H or C 1 -C 1.
3 represents an alkyl group. Acylation with a fatty acid or an ester thereof (hereinafter abbreviated as “fatty acid or ester (V)”) thereof to obtain an amine (I).
【００１４】本発明のアミン（Ｉ）の製造法について更
に詳細に説明する。アミノアルコール（II）のアクリロ
ニトリルを用いるシアノエチル化反応において、アミノ
アルコール（II）に対して 0.8〜２倍モルのアクリロニ
トリルを50〜70℃に保ちながら添加し、１〜５時間かけ
て反応を終了させ、シアノエチル化物を得る。このシア
ノエチル化物をNi等の触媒の存在下、60〜120 ℃、１〜
20時間かけて水素化反応を行い、アミノアルコール(II
I) を得る。必要とあれば、アクリロニトリルを用いる
シアノエチル化反応及び水素化反応を繰り返し、アミノ
アルコール (IV) を得る。得られたアミノアルコール(I
II) 又は (IV) に、アミノアルコール(III) 又は (IV)
に対して 1.8〜２倍モルの脂肪酸もしくはそのエステル
（Ｖ）を用いて無触媒または触媒存在下、 100〜220 ℃
で１〜24時間かけて常圧もしくは減圧下でアシル化を行
い、アミン（Ｉ）を得る。The process for producing the amine (I) of the present invention will be described in more detail. In the cyanoethylation reaction of amino alcohol (II) using acrylonitrile, 0.8 to 2 moles of acrylonitrile relative to amino alcohol (II) is added while maintaining the temperature at 50 to 70 ° C., and the reaction is completed in 1 to 5 hours. To give the cyanoethylated product. This cyanoethylated product is reacted at 60 to 120 ° C. for 1 to 1 in the presence of a catalyst such as Ni.
The hydrogenation reaction is carried out for 20 hours, and the amino alcohol (II
I) get If necessary, the cyanoethylation reaction and the hydrogenation reaction using acrylonitrile are repeated to obtain amino alcohol (IV). The obtained amino alcohol (I
(II) or (IV) with amino alcohol (III) or (IV)
100 to 220 ° C. in the absence or presence of a catalyst using 1.8 to 2 moles of a fatty acid or its ester (V) to
For 1 to 24 hours under normal pressure or reduced pressure to obtain the amine (I).
【００１５】本発明においてアシル化に使用される脂肪
酸もしくはそのエステル（Ｖ）としては、オクタン酸、
デカン酸、ドデカン酸、テトラデカン酸、ヘキサデカン
酸、オクタデカン酸、エイコサン酸、ドコサン酸、２−
エチルヘキサン酸、２−ブチルオクタン酸、２−ヘキシ
ルデカン酸、２−オクチルドデカン酸、２−デシルテト
ラデカン酸、２−ドデシルヘキサデカン酸、２−テトラ
デシルオクタデカン酸、２−ヘキサデシルエイコサン酸
あるいはこらの脂肪酸のメチルエステル、エチルエステ
ル、プロピルエステルなど、またはこれらの混合物が挙
げられる。本発明のアシル化に使用される触媒として
は、ナトリウムメチラート、ナトリウムエチラート、カ
リウムメチラート、水酸化ナトリウム、水酸化カリウム
などが挙げられる。In the present invention, the fatty acid or its ester (V) used for acylation includes octanoic acid,
Decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, eicosanoic acid, docosanoic acid, 2-
Ethylhexanoic acid, 2-butyloctanoic acid, 2-hexyldecanoic acid, 2-octyldodecanoic acid, 2-decyltetradecanoic acid, 2-dodecylhexadecanoic acid, 2-tetradecyloctadecanoic acid, 2-hexadecyleicosanoic acid or the like Examples include fatty acid methyl esters, ethyl esters, propyl esters, and the like, or mixtures thereof. The catalyst used in the acylation of the present invention includes sodium methylate, sodium ethylate, potassium methylate, sodium hydroxide, potassium hydroxide and the like.
【００１６】本発明のアミン（Ｉ）は赤外吸収スペクト
ル、核磁気共鳴スペクトルでその構造を確認することが
できる。The structure of the amine (I) of the present invention can be confirmed by infrared absorption spectrum and nuclear magnetic resonance spectrum.
【００１７】[0017]
【実施例】以下、実施例により本発明を更に詳細に説明
するが、本発明はこれらに限定されるものではない。EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the present invention is limited thereto.
【００１８】実施例１ 攪拌機、温度計、滴下ロートを備えた４つ口フラスコに
２−ピペリジンエタノール 201ｇを入れ、60℃まで昇温
した。液温を55〜65℃に保ちながら、３時間かけてアク
リロニトリル99.4ｇを滴下した。反応終了後、反応液 2
12ｇを攪拌機、温度計、圧力計を備えたオートクレーブ
に移した。続いてラネーNi 10.6 ｇを添加し、水素圧20
kg／cm2G、温度を70℃に保ちながら14時間かけて水素化
反応を行った。反応終了後、ラネーNiを濾過し、反応液
を蒸留して78ｇのアミノアルコールを得た。沸点 142〜
150 ℃／２Torr。攪拌機、温度計、脱水管を備えた４つ
口フラスコに上記のアミノアルコール61ｇとオクタデカ
ン酸 161ｇを入れ、 180℃まで昇温した。そのままの温
度で15時間、生成する水を留去しながらアシル化反応を
行い、目的物を 195ｇ得た。1H−NMR スペクトル、IRス
ペクトルから以下の構造を確認した。Example 1 201 g of 2-piperidineethanol was placed in a four-necked flask equipped with a stirrer, a thermometer, and a dropping funnel, and heated to 60 ° C. While maintaining the liquid temperature at 55 to 65 ° C., 99.4 g of acrylonitrile was added dropwise over 3 hours. After the reaction is completed,
12 g was transferred to an autoclave equipped with a stirrer, thermometer and pressure gauge. Subsequently, Raney Ni (10.6 g) was added, and the hydrogen pressure was increased to 20.
The hydrogenation reaction was performed for 14 hours while maintaining the temperature at 70 ° C. in kg / cm 2 G. After completion of the reaction, Raney Ni was filtered and the reaction solution was distilled to obtain 78 g of amino alcohol. Boiling point 142 ~
150 ° C / 2 Torr. 61 g of the above-mentioned amino alcohol and 161 g of octadecanoic acid were placed in a four-necked flask equipped with a stirrer, a thermometer and a dehydrating tube, and the temperature was raised to 180 ° C. The acylation reaction was carried out at the same temperature for 15 hours while distilling off the produced water to obtain 195 g of the desired product. The following structure was confirmed from the 1 H-NMR spectrum and the IR spectrum.
【００１９】[0019]
【化１０】 Embedded image
【００２０】・IRスペクトル 1731cm-1、1641cm-1、1541cm-1、1467cm-1 実施例２ 攪拌機、温度計、滴下ロートを備えた４つ口フラスコに
３−ヒドロキシピロリジン 220ｇを入れ、60℃まで昇温
した。液温を55〜65℃に保ちながら、３時間かけてアク
リロニトリル 161ｇを滴下した。反応終了後、反応液を
攪拌機、温度計、圧力計を備えたオートクレーブに移し
た。続いてラネーNi 17.7 ｇを添加し、水素圧20kg／cm
2G、温度を70℃に保ちながら14時間かけて水素化反応を
行った。反応終了後、ラネーNiを濾過し、反応液を蒸留
して 182ｇのアミノアルコールを得た。攪拌機、温度
計、滴下ロートを備えた４つ口フラスコに上記のアミノ
アルコール160 ｇを入れ、60℃まで昇温した。液温を55
〜65℃に保ちながら、３時間かけてアクリロニトリル5
8.9ｇを滴下した。反応終了後、反応液を攪拌機、温度
計、圧力計を備えたオートクレーブに移した。続いてラ
ネーNi 10.9 ｇを添加し、水素圧20kg／cm2G、温度を70
℃に保ちながら14時間かけて水素化反応を行った。反応
終了後、ラネーNiを濾過し、反応液を蒸留して 110ｇの
アミノアルコールを得た。攪拌機、温度計、滴下ロート
を備えた４つ口フラスコに上記のアミノアルコール110
ｇを入れ、60℃まで昇温した。液温を55〜65℃に保ちな
がら、３時間かけてアクリロニトリル22.9ｇを滴下し
た。反応終了後、反応液を攪拌機、温度計、圧力計を備
えたオートクレーブに移した。続いてラネーNi 6.6ｇを
添加し、水素圧20kg／cm2G、温度を70℃に保ちながら14
時間かけて水素化反応を行った。反応終了後、ラネーNi
を濾過し、反応液を蒸留して66.4ｇのアミノアルコール
を得た。攪拌機、温度計、脱水管を備えた４つ口フラス
コに上記のアミノアルコール61ｇとオクタデカン酸 133
ｇとナトリウムメチラート 0.3ｇを入れ、 180℃まで昇
温した。そのままの温度で18時間、生成するメタノール
を留去しながらアシル化反応を行い、目的物を 165ｇ得
た。1H−NMR スペクトル、IRスペクトルから以下の構造
を確認した。IR spectrum 1731 cm -1 , 1641 cm -1 , 1541 cm -1 , 1467 cm -1 Example 2 220 g of 3-hydroxypyrrolidine was placed in a four-necked flask equipped with a stirrer, thermometer, and dropping funnel, and heated to 60 ° C. The temperature rose. While maintaining the liquid temperature at 55 to 65 ° C, 161 g of acrylonitrile was added dropwise over 3 hours. After the completion of the reaction, the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge. Subsequently, 17.7 g of Raney Ni was added, and the hydrogen pressure was 20 kg / cm.
The hydrogenation reaction was performed for 14 hours while maintaining the temperature at 2 G and 70 ° C. After completion of the reaction, Raney Ni was filtered and the reaction solution was distilled to obtain 182 g of amino alcohol. 160 g of the above amino alcohol was placed in a four-necked flask equipped with a stirrer, a thermometer, and a dropping funnel, and the temperature was raised to 60 ° C. Liquid temperature 55
Acrylonitrile 5 over 3 hours while maintaining ~ 65 ° C
8.9 g was added dropwise. After the completion of the reaction, the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge. Subsequently, 10.9 g of Raney Ni was added, the hydrogen pressure was 20 kg / cm 2 G, and the temperature was 70 ° C.
The hydrogenation reaction was performed for 14 hours while maintaining the temperature. After completion of the reaction, Raney Ni was filtered and the reaction solution was distilled to obtain 110 g of amino alcohol. The amino alcohol 110 was placed in a four-necked flask equipped with a stirrer, thermometer, and dropping funnel.
g was added and the temperature was raised to 60 ° C. While maintaining the liquid temperature at 55 to 65 ° C, 22.9 g of acrylonitrile was added dropwise over 3 hours. After the completion of the reaction, the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge. Subsequently, 6.6 g of Raney Ni was added, and while maintaining the hydrogen pressure at 20 kg / cm 2 G and the temperature at 70 ° C., 14
The hydrogenation reaction was performed over time. After the reaction, Raney Ni
Was filtered, and the reaction solution was distilled to obtain 66.4 g of amino alcohol. In a four-necked flask equipped with a stirrer, a thermometer, and a dehydrating tube, 61 g of the above amino alcohol and 133 octadecanoic acid were added.
g and 0.3 g of sodium methylate were added, and the temperature was raised to 180 ° C. The acylation reaction was carried out at the same temperature for 18 hours while distilling off the produced methanol to obtain 165 g of the desired product. The following structure was confirmed from the 1 H-NMR spectrum and the IR spectrum.
【００２１】[0021]
【化１１】 Embedded image
【００２２】・IRスペクトル 1734cm-1、1638cm-1、1541cm-1、1464cm-1 実施例３ 攪拌機、温度計、滴下ロートを備えた４つ口フラスコに
Ｎ−（２−ヒドロキシエチル）ピペラジン 290ｇを入
れ、60℃まで昇温した。液温を55〜65℃に保ちながら、
３時間かけてアクリロニトリル118ｇを滴下した。反応
終了後、反応液392ｇを攪拌機、温度計、圧力計を備え
たオートクレーブに移した。続いてラネーNi19.6ｇを添
加し、水素圧20kg／cm2G、温度を70℃に保ちながら10時
間かけて水素化反応を行った。反応終了後、ラネーNiを
濾過し、反応液を蒸留して 263ｇのアミノアルコールを
得た。沸点 148〜153 ℃／５Torr。攪拌機、温度計、脱
水管を備えた4つ口フラスコに上記のアミノアルコール1
06ｇとオクタデカン酸 278ｇを入れ、 180℃まで昇温し
た。そのままの温度で24時間、生成する水を留去しなが
らアシル化反応を行い、目的物を 366ｇ得た。1H−NMR
スペクトル、IRスペクトルから以下の構造を確認した。IR spectrum 1734 cm -1 , 1638 cm -1 , 1541 cm -1 , 1464 cm -1 Example 3 290 g of N- (2-hydroxyethyl) piperazine was placed in a four-necked flask equipped with a stirrer, thermometer and dropping funnel. And heated to 60 ° C. While keeping the liquid temperature at 55-65 ° C,
118 g of acrylonitrile was added dropwise over 3 hours. After the completion of the reaction, 392 g of the reaction solution was transferred to an autoclave equipped with a stirrer, thermometer, and pressure gauge. Subsequently, 19.6 g of Raney Ni was added, and a hydrogenation reaction was carried out for 10 hours while maintaining the hydrogen pressure at 20 kg / cm 2 G and the temperature at 70 ° C. After completion of the reaction, Raney Ni was filtered, and the reaction solution was distilled to obtain 263 g of amino alcohol. Boiling point 148-153 ° C / 5 Torr. The above amino alcohol 1 was placed in a four-necked flask equipped with a stirrer, thermometer and dehydration tube.
06 g and 278 g of octadecanoic acid were added, and the temperature was raised to 180 ° C. The acylation reaction was carried out at the same temperature for 24 hours while distilling off the produced water to obtain 366 g of the desired product. 1 H-NMR
The following structures were confirmed from the spectrum and the IR spectrum.
【００２３】[0023]
【化１２】 Embedded image
【００２４】・IRスペクトル 1728cm-1、1635cm-1、1545cm-1、1467cm-1 実施例４ 攪拌機、温度計、圧力計を備えたオートクレーブにピペ
ラジン 172ｇを入れ、90〜100 ℃に保ちながら９−クロ
ロノナノール 286ｇとエタノール20％水溶液を２時間か
けて滴下した後、更に50％水酸化ナトリウム水溶液 134
ｇを５時間かけて圧入し、100 ℃のまま８時間熟成を行
い付加反応を完了させた。反応終了後、反応液を、液が
中性になるまで水で洗浄した後、蒸留により 137ｇのＮ
−（９−ヒドロキシノニル）ピペラジンを得た。攪拌
機、温度計、滴下ロートを備えた４つ口フラスコに上記
のＮ−（９−ヒドロキシノニル）ピペラジン120 ｇを入
れ60℃まで昇温した。液温を55〜65℃に保ちながら４時
間かけてアクリロニトリル28ｇを滴下した。反応終了
後、反応液を攪拌機、温度計、圧力計を備えたオートク
レーブに移した。続いてラネーＮｉ ７．４ｇを添加
し、水素圧２０ｋｇ／cm2G、温度を70℃に保ちながら25
時間かけて水素化反応を行った。反応終了後、ラネーNi
を濾過し、反応液を蒸留して89.4ｇのアミノアルコール
を得た。攪拌機、温度計、脱水管を備えた４つ口フラス
コに上記のアミノアルコール80ｇとオクタデカン酸 146
ｇを入れ、 180℃まで昇温した。そのままの温度で18時
間、生成する水を留去しながらアシル化反応を行い、目
的物を 202ｇ得た。1H−NMR スペクトル、IRスペクトル
から以下の構造を確認した。IR spectrum 1728 cm -1 , 1635 cm -1 , 1545 cm -1 , 1467 cm -1 Example 4 172 g of piperazine was placed in an autoclave equipped with a stirrer, thermometer, and pressure gauge, and the temperature was maintained at 90-100 ° C. After 286 g of chlorononanol and a 20% aqueous solution of ethanol were added dropwise over 2 hours, a 50% aqueous solution of sodium hydroxide was further added.
g was injected over 5 hours, and aged at 100 ° C. for 8 hours to complete the addition reaction. After completion of the reaction, the reaction solution was washed with water until the solution became neutral, and then 137 g of N was distilled off.
-(9-Hydroxynonyl) piperazine was obtained. In a four-necked flask equipped with a stirrer, a thermometer and a dropping funnel, 120 g of the above-mentioned N- (9-hydroxynonyl) piperazine was charged and the temperature was raised to 60 ° C. While maintaining the liquid temperature at 55 to 65 ° C, 28 g of acrylonitrile was added dropwise over 4 hours. After the completion of the reaction, the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge. Subsequently, 7.4 g of Raney Ni was added, and while maintaining the hydrogen pressure at 20 kg / cm 2 G and the temperature at 70 ° C., 25 g was added.
The hydrogenation reaction was performed over time. After the reaction, Raney Ni
Was filtered and the reaction solution was distilled to obtain 89.4 g of amino alcohol. In a four-necked flask equipped with a stirrer, a thermometer and a dehydrating tube, 80 g of the above amino alcohol and octadecanoic acid 146 were added.
g was added and the temperature was raised to 180 ° C. An acylation reaction was carried out at the same temperature for 18 hours while distilling off generated water to obtain 202 g of the desired product. The following structure was confirmed from the 1 H-NMR spectrum and the IR spectrum.
【００２５】[0025]
【化１３】 Embedded image
【００２６】・IRスペクトル 1728cm-1、1635cm-1、1545cm-1、1467cm-1 IR spectrum 1728 cm -1 , 1635 cm -1 , 1545 cm -1 , 1467 cm -1
【００２７】[0027]
【発明の効果】本発明のアミンは、柔軟性に優れかつ生
分解性のより優れた界面活性剤として有用であり、特に
布、毛髪などの柔軟剤として極めて有用である。The amine of the present invention is useful as a surfactant having excellent flexibility and biodegradability, and is particularly useful as a softener for fabric, hair and the like.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ Ｃ０７Ｄ 295/08 Ｃ０７Ｄ 295/08 Ａ // Ｃ０７Ｂ 61/00 ３００ Ｃ０７Ｂ 61/00 ３００ (58)調査した分野(Int.Cl.7，ＤＢ名) C07D 207/08 C07D 207/12 C07D 211/22 C07D 295/08 B01F 17/22 B01J 25/02 ＣＡ（ＳＴＮ) ＣＡＯＬＤ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. 7 Identification symbol FI C07D 295/08 C07D 295/08 A // C07B 61/00 300 C07B 61/00 300 (58) Investigated field (Int.Cl. 7 , DB name) C07D 207/08 C07D 207/12 C07D 211/22 C07D 295/08 B01F 17/22 B01J 25/02 CA (STN) CAOLD (STN) REGISTRY (STN)
Claims (2)
基又はアルケニル基を示し、２つのR1は同一でも異なっ
ていても良い。 X ：−CR＜又は−N＜を示す。ここでRはH 又は炭素数１
〜４のアルキル基を示す。 k ：１〜３の数を示す。 p ：０〜９の数を示す。 m、n ：同一又は異なって０〜４の数を示す。但し m及
びn が同時に０になることはない。〕1. An amine represented by the general formula (I). Embedded image [In the formula, R 1 represents a linear or branched alkyl group or alkenyl group having 7 to 35 carbon atoms, and two R 1 may be the same or different. X: represents -CR <or -N <. Where R is H or carbon number 1
And represents alkyl groups 4 to 4. k: Indicates the number of 1 to 3. p: Indicates the number of 0-9. m, n: same or different, and represents a number of 0-4. However, m and n do not become 0 at the same time. ]
れるアミノアルコールをシアノエチル化後、水素化反応
を行い、一般式（ＩＩＩ） 【化３】 〔式中、Ｘ 、p 、m 、n は前記の意味を示す。〕で表
されるアミノアルコールとし、要すればシアノエチル化
反応及び水素化反応を繰り返し一般式（IV） 【化４】 〔式中、X 、p 、m 、n は前記の意味を示し、q は２〜
３の数を示す。〕で表されるアミノアルコールとし、得
られた一般式(III) 又は (IV) で表されるアミノアルコ
ールを一般式（Ｖ） R1COOR2 （Ｖ） 〔式中、R1は前記の意味を示し、R2はH 又は炭素数１〜
３のアルキル基を示す。〕で表される脂肪酸又はそのエ
ステルでアシル化することを特徴とする、請求項１記載
の一般式（Ｉ）で表されるアミンの製造法。2. A compound of the general formula (II) [Wherein, X, p, m, and n have the same meaning as described above. After cyanoethylation of the amino alcohol represented by the general formula (III) [Wherein, X, p, m, and n have the above-mentioned meanings. And repeating, if necessary, a cyanoethylation reaction and a hydrogenation reaction, in the general formula (IV): [Wherein, X, p, m, and n represent the above-mentioned meanings, and q represents 2 to
Shows the number 3. And the resulting amino alcohol represented by the general formula (III) or (IV) is represented by the general formula (V) R 1 COOR 2 (V) wherein R 1 is as defined above. Wherein R 2 is H or has 1 to 1 carbon atoms.
3 represents an alkyl group. The method for producing an amine represented by the general formula (I) according to claim 1, wherein the acylation is carried out with a fatty acid or an ester thereof represented by the following formula:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04175264A JP3081065B2 (en) | 1992-07-02 | 1992-07-02 | Novel amine and its production method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04175264A JP3081065B2 (en) | 1992-07-02 | 1992-07-02 | Novel amine and its production method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0616623A JPH0616623A (en) | 1994-01-25 |
| JP3081065B2 true JP3081065B2 (en) | 2000-08-28 |
Family
ID=15993116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP04175264A Expired - Lifetime JP3081065B2 (en) | 1992-07-02 | 1992-07-02 | Novel amine and its production method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3081065B2 (en) |
-
1992
- 1992-07-02 JP JP04175264A patent/JP3081065B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0616623A (en) | 1994-01-25 |
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